9880. Uridine 5′-Triphosphate

Nomenclature

CAS number: 63-39-8
Uridine 5′-(tetrahydrogen triphosphate); UTP.
C9H15N2O15P3; mol wt 484.14.
C 22.33%, H 3.12%, N 5.79%, O 49.57%, P 19.19%.

Description and references

Pyrimidine analog of ATP. Activates chloride channels in epithelial cells; increases ciliary beat frequency and induces degranulation of goblet cells in airway epithelia. Also effects inflammatory cell function and vascular reactivity. Isoln from rabbit muscle: Lipton et al., J. Am. Chem. Soc. 75, 5450 (1953). Synthesis: Kenner et al., J. Chem. Soc. 1954, 2288; Hall, Khorana, J. Am. Chem. Soc. 76, 5056 (1954). Review of bioactivity mediated by nucleotide receptors: S. E. O'Connor, Life Sci. 50, 1657-1664 (1992). Clinical effect on chloride secretion in cystic fibrosis: M. R. Knowles et al., Am. J. Respir. Crit. Care Med. 151, S65 (1995); on mucociliary clearance in combination with amiloride, q.v.: W. D. Bennett et al., ibid. 153, 1796 (1996).

Chemical structure

Derivative

Trisodium salt dihydrate.

Nomenclature

Uteplex (Am. Home).
C9H12N2Na3O15P3.2H2O; mol wt 586.12.
C 18.44%, H 2.75%, N 4.78%, Na 11.77%, O 46.41%, P 15.85%.

Properties

White powder, sol in water, very sparingly sol in alcohol. pKa1 6.6; pKa2 9.5. uv max (pH 7): 262 nm (aM 10,000); (pH 11): 261 nm (aM 8100).

Therapeutic Category

In treatment of cystic fibrosis.